From side streets to the trails, take the force out cold winds with the Kuhl Men's Impakt Jacket. In addition to being sleek and soft, the polyester Softschell fabric offers windproof and water resistant protection against the elements. Plus, the grid fleece backer beneath the arms improves ventilation for when you work up a sweat.
REI La Selva Rain Jacket length black rain trenches are classy enough for a restaurant, dress up a tee and leggings, and are GREAT in rain. I have a LL Bean version that I love [currently out of stock, but highly recommend].